Great, so now my card's getting shut down by a fraud department for "suspicious activity." Plus the prepaid card I bought got drained before I could use it, so now I not only don't have a card I actually want, but I'm out the money I spent as well. Sounds like a great plan!

Exactly. Even without the pitfalls, at the end of the day doing the gift card conversions is very much getting into the "game" aspect of the points/cash back hobby that many of us here enjoy. If it's not fun for someone (and it doesn't sound fun to me,) then I think it's fair for someone to just take the easy path, particularly when that easy path also offers some rewards. There's a fairly large time investment involved in learning how best to do it, how not to get flagged, how to avoid getting a card that's drained before you can use it, getting to the stores, etc. plus the cost of getting to all the places needed to make it work optimally. Even with a car, gas prices are high and maintenance is no joke either. I'd rather enjoy my time doing other things at that point, especially since I'd be paranoid about all the pitfalls.